Honest answers.

Would you date someone from your past that you never really dated or talked to much because she had a bit of a wild side?

I’m talking about someone who dated a lot of football players, went to parties all the time, and lived that kind of lifestyle. Now, years later, she has a kid or two and starts talking to you. She tells you that she overlooked you in high school because you were quiet and shy and didn’t seem very interesting back then. But now that y’all are older, she says she can see herself being with you because you’re stable, mature, and more grown up.

My question is: would you date her as a single mom with kids? Do you think it’s harder to settle down with someone who already has children compared to someone who doesn’t? And does a person’s past history play a role in your decision?